Autologous tooth transplantation is the transplantation of an erupted, partially erupted, or unerupted tooth from one site to another in an individual. This is expected to maintain alveolar bone volume through physiological stimulation of the periodontal ligament (PDL). Tooth transplantation can be used for the closure of oroantral communication. As a simple, useful, and minimally invasive method, it should be considered a surgical option when a donor tooth is available in indicated cases. Herein, the authors report the case of a 20-year-old female patient whose left permanent maxillary first molar had to be extracted due to a longitudinal fracture and radicular cyst in the maxillary sinus floor. After the extraction, tooth 28 was exposed through an osteotomy and positioned in the gap. Nineteen years later, the autologous grafted tooth 28 could no longer be retained due to massive external resorption and was replaced by an implant. Human PDL stem cells can differentiate into bone-, fiber-, and cementum-forming cells and have the potential to build a PDL complex. Therefore, care must be taken to avoid damaging the PDL of the donor tooth during extraction. Autotransplanted teeth are expected to retain the alveolar bone volume. This case demonstrates the use of a transplanted tooth 28 for the treatment of a maxillary defect caused by the extraction of tooth 26 and removal of a radicular cyst. External resorption and regeneration of the bone of the maxillary sinus floor around the transplanted tooth occurred after 19 years.